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"Save checklist data to Jira custom fields" option must be enabled in Issue Checklist Global Settings. 

Step by step guide

1. Create a new rule in Automation plugin rule (go to Project Settings > Project automation Automation and click Create rule button)
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2. Select "Issue TransitionTransitioned" as a trigger and next choose source and destination statuses (details of transition)
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3. Select Action as the next step and choose "Edit Issue" from the list of actions
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4. Select Checklist Content YAML field Text field on the next screen
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5. Paste checklist in YAML text format as presented on the screenshot, i.e.:

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   No Format
   - text: 'Acceptance criteria 1' checked: false - text: 'Acceptance criteria 2' checked: false

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   title	Read more about YAML

   Include PageCreate YAML for a checklistCreate YAML for a checklist

   
   

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   Info
   If you want to append checklist items, then put Checklist Content YAML Text field ID in double curly braces instead "items:" phrase in as the first line, before new items, as explained in separate documentation page.

   
   

6. Save the rule and test your setup (transition an issue, refresh the page and spot the checklist updated)
   
   

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   title If it doesn't work, read this
   If the checklist is not updated then, please add Checklist Content YAML (or Checklist Text ) custom field to issue screen and check if it is correctly updated when the issue is transitioned. If the Checklist Content YAML (or Checklist Text ) field is not updated (its content does not change) then please check the created rule, especially step 2 (source and destination transition) as the rule might not be started for a given transition. If the Checklist Content YAML (or Checklist Text ) field is updated but the checklist panel (list of checkboxes) does not, then one of the following can be a reason:most likely custom fields integration is not enabled (please enable it)the YAML provided in step 5 is invalid so it cannot be parsed and translated to the list of checkboxes. Consider using Checklist Text field (which is simpler for human interaction) or read more about YAML.

   
   

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   title Read why page refresh is required to see the checklist
   The following happens in the background: Issue is transitioned Jira sends a webhook notification to Automation plugin (this is asynchronous; usually 1 to 3 seconds but might take significantly more time) Automation plugin does its job (updates issue by setting the checklist field) When the issue is updated (checklist field), Jira sends a webhook notification to Checklist plugin (again, this is asynchronous; usually 1 to 3 seconds but might take significantly more time) Checklist plugin reads checklist text field and transforms it into the checklist that you can see in the UI (this is synchronous and almost instant 1-3 seconds) The above means that: The issue page needs to be refreshed to see the checklist (because the process described in the list above is not finished yet when the issue page is loaded after transition - that is how plugins work in Jira Cloud). On average, few seconds after transition are required to see the checklist in the UI (so usually the first page refresh after transition shows checklist already) In rare cases, it might take longer to see the checklist (dozen of seconds or a couple of minutes so keep refreshing the issue page)